Versatile and practical chiral shift reagent with hydrogen-bond donor/acceptor sites in a macrocyclic cavity

Tadashi Ema; Daisuke Tanida; Takashi Sakai

doi:10.1021/ol0613665

Versatile and practical chiral shift reagent with hydrogen-bond donor/acceptor sites in a macrocyclic cavity

Tadashi Ema, Daisuke Tanida, Takashi Sakai

Research output: Contribution to journal › Article › peer-review

70 Citations (Scopus)

Abstract

Bifunctional macrocycle 1 with C₂ symmetry was newly synthesized. NMR studies demonstrated that receptor 1 functions as a chiral shift reagent (solvating agent) that is highly effective for a wide range of chiral compounds having a carboxylic acid, oxazolidinone, lactone, alcohol, sulfoxide, sulfoximine, isocyanate, or epoxide functionality. Binding constants were determined to investigate the binding behavior of 1.

Original language	English
Pages (from-to)	3773-3775
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	17
DOIs	https://doi.org/10.1021/ol0613665
Publication status	Published - Aug 17 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol0613665

Cite this

@article{dac12ae3b8ca47429f2e261775ae74d0,

title = "Versatile and practical chiral shift reagent with hydrogen-bond donor/acceptor sites in a macrocyclic cavity",

abstract = "Bifunctional macrocycle 1 with C2 symmetry was newly synthesized. NMR studies demonstrated that receptor 1 functions as a chiral shift reagent (solvating agent) that is highly effective for a wide range of chiral compounds having a carboxylic acid, oxazolidinone, lactone, alcohol, sulfoxide, sulfoximine, isocyanate, or epoxide functionality. Binding constants were determined to investigate the binding behavior of 1.",

author = "Tadashi Ema and Daisuke Tanida and Takashi Sakai",

year = "2006",

month = aug,

day = "17",

doi = "10.1021/ol0613665",

language = "English",

volume = "8",

pages = "3773--3775",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Versatile and practical chiral shift reagent with hydrogen-bond donor/acceptor sites in a macrocyclic cavity

AU - Ema, Tadashi

AU - Tanida, Daisuke

AU - Sakai, Takashi

PY - 2006/8/17

Y1 - 2006/8/17

N2 - Bifunctional macrocycle 1 with C2 symmetry was newly synthesized. NMR studies demonstrated that receptor 1 functions as a chiral shift reagent (solvating agent) that is highly effective for a wide range of chiral compounds having a carboxylic acid, oxazolidinone, lactone, alcohol, sulfoxide, sulfoximine, isocyanate, or epoxide functionality. Binding constants were determined to investigate the binding behavior of 1.

AB - Bifunctional macrocycle 1 with C2 symmetry was newly synthesized. NMR studies demonstrated that receptor 1 functions as a chiral shift reagent (solvating agent) that is highly effective for a wide range of chiral compounds having a carboxylic acid, oxazolidinone, lactone, alcohol, sulfoxide, sulfoximine, isocyanate, or epoxide functionality. Binding constants were determined to investigate the binding behavior of 1.

UR - http://www.scopus.com/inward/record.url?scp=33748616549&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748616549&partnerID=8YFLogxK

U2 - 10.1021/ol0613665

DO - 10.1021/ol0613665

M3 - Article

C2 - 16898814

AN - SCOPUS:33748616549

SN - 1523-7060

VL - 8

SP - 3773

EP - 3775

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Versatile and practical chiral shift reagent with hydrogen-bond donor/acceptor sites in a macrocyclic cavity

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this